Selective rearrangements of quadruply hydrogen-bonded dimer driven by donor-acceptor interaction

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	Selective rearrangements of quadruply hydrogen-bonded dimer driven by donor-acceptor interaction
	Wang XZ(王晓钟) ; Li XQ(李晓强) ; Shao XB(邵学斌) ; Zhao X(赵新) ; Deng P(邓鹏) ; Jiang XK(蒋锡夔) ; Li ZT(黎占亭) ; Chen YQ(陈英奇)
刊名	Chem.-Eur. J.
	2003
卷号	9 期号:12 页码:2904-2913
ISSN号	0947-6539
其他题名	供体受体相互作用驱动的四氢键二聚体的选择性重排
通讯作者	黎占亭
英文摘要	developed to control the selective rear-rangement of Meijer's AADD quadruply hydrogen-bonded homodimers by introducing an additional donor-acceptor interaction. 'fherefore, one donor-assembling monomer, 1, in which the electron-rich bis(p-phenylene)-3crown-1O moiety is connected to the hydrogen-bonding moiety, and two acceptor-assembling monomers, 2 and 3, in which the electron-deficient pyromellitic diimide or naphthalene diimide group is incorporated, respectively, are synthesized and characterized. IH NMR and 2D-NOESY tudies show that all these compounds exist as stable homodimers in chloroform. Mixing t equiv of t with l equiv of 2 in chloroform leads to the formation of heterodimers 1.2 in≈60% yield, as a result of the electrostatic interaction between the bis(P-phenylene)-34-crown-IO moiety of 1 and the pyromellitic diimide group of 2. Selective formation of heterodimer 1 .3 (>97%) was achieved by mixing l equiv of 1 with l equiv of 3 in chloroform which resulted in a strengthened electrostatic interaction between the bis(p-phenylene)-[34]crown-1O moiety of l and the naphthalene diimide group of 3. The structures of heterodimers 1.2 and 1.3, which have been characterized by 1H NMR and UV/Vis experiments, reveal a remarkable promoting effect between the donor-acceptor interaction and intermolecular hydrogen-bond- ing. 1H NMR studies also reveal that heterodimers 1.2 and 1.3 can be fullyand partially dissociated by addition of heterocycle 29, leading to the formation of new more robust heterodimers 1.29 and 2.29, or 3.29,respectively, and partially regenerated by subsequent addition of heterocyclic compound 30 through the formation of a new heterodimer 29.30. Heterodimers 1.2 and 1.3 represent a novel class of pseudo[2]ro-taxanes constructed by two different noncovalent interactions.
学科主题	物理有机化学
收录类别	SCI
原文出处	http://dx.doi.org/10.1002/chem.200204513
语种	英语
WOS记录号	WOS:000183712300026
公开日期	2013-01-16
内容类型	期刊论文
源URL	[http://202.127.28.38/handle/331003/12638]
专题	上海有机化学研究所_物理有机化学研究室
推荐引用方式 GB/T 7714	Wang XZ,Li XQ,Shao XB,et al. Selective rearrangements of quadruply hydrogen-bonded dimer driven by donor-acceptor interaction[J]. Chem.-Eur. J.,2003,9(12):2904-2913.
APA	王晓钟.,李晓强.,邵学斌.,赵新.,邓鹏.,...&陈英奇.(2003).Selective rearrangements of quadruply hydrogen-bonded dimer driven by donor-acceptor interaction.Chem.-Eur. J.,9(12),2904-2913.
MLA	王晓钟,et al."Selective rearrangements of quadruply hydrogen-bonded dimer driven by donor-acceptor interaction".Chem.-Eur. J. 9.12(2003):2904-2913.